3-tert-butoxycarbonyl-7-chloro-6-(3-fluoro-4-isopropylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 7-chloro-6-(3-fluoro-4-isopropylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 2041545Notes

Reaction equation

HRID 2041545 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:33])[NH:29][CH:30]([CH3:32])[CH3:31])=[C:24]([F:34])[CH:23]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=O)(C)(C)C>O1CCOCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:11]2[CH2:10][CH2:9][NH:8][CH2:14][CH2:13][C:12]=2[C:15]=1[NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:33])[NH:29][CH:30]([CH3:32])[CH3:31])=[C:24]([F:34])[CH:23]=1

Participants

3

Reactant 1

HCID 576564403-tert-butoxycarbonyl-7-chloro-6-(3-fluoro-4-isopropylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 576565617-chloro-6-(3-fluoro-4-isopropylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Use a method similar to the General Procedure 1-4 to deprotect 3-tert-butoxycarbonyl-7-chloro-6-(3-fluoro-4-isopropylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.406 g, 0.83 mmol) in 1,4-dioxane (12.8 mL). Purify by SCX chromatography eluting with dichloromethane and dichloromethane/2M ammonia in methanol (1:1) followed by chromatography on silica gel (40 g RediSep column) eluting with dichloromethane/2M ammonia in methanol (99:1 to 90:10 over 30 min) and then dichloromethane/2M ammonia in methanol (90:10 over 30 min; 35 mL/min) to afford 7-chloro-6-(3-fluoro-4-isopropylcarbamoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a colorless oil (0.3237 g). MS (ES+) m/z: 390.1 (M+H)+. Use a method similar to the General Procedure 2-1, using 7-chloro-6-(3-fluoro-4-isopropylcarbanzoyl-benzylamino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.301 g, 0.772 mmol) to provide the title compound as a beige solid (0.328 g, 84%). MS (ES+) m/z: 390.1 (M+H)+.

Workup

  1. customPurify by SCX chromatography
  2. washeluting with dichloromethane and dichloromethane/2M ammonia in methanol (1:1)
  3. washeluting with dichloromethane/2M ammonia in methanol (99:1 to 90:10 over 30 min)

Sources & evidence

ORD record
ord-a691289c60f048bbaf299ea12dad8a98
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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